10 Most Embarrassing Moments Of Triple H's Career

The legendary career of Triple H has seen him thriving in the wrestling business for almost three decades. Vince McMahon saw something special in Triple H, signing him away from WCW during the New Generation Era. Triple H delivered successful results in various chapters of his career, ranging from D-Generation X to Evolution to hitting legend status.

However, there were quite a few moments that he likely regrets given how weak they turned out. Even the biggest stars like Triple H are prone to having their fair share of bad times. This proves that no one is perfect, as the bad can sometimes outweigh the positive in some scenarios. The following moments were the most embarrassing of Triple H’s career.

10 Hog Pen Match

The rivalry between Triple H and Henry Godwinn was one of the worst of Triple H’s career. WWE was trying to give both wrestlers an angle to build momentum when the company struggled to build new stars.

Godwinn’s gimmick of a pig farmer led to Triple H getting placed in a Hog Pen match against him. The finish saw Triple H winning by throwing Godwinn in a Hog Pen, but both wrestlers were embarrassed by this match. One fun moment came backstage when Owen Hart told the handler that the pigs should be placed in Vince McMahon’s office before showtime.

9 Losing The WWE Championship To Hulk Hogan

Triple H returning to WWE in 2002 as a huge face provided one of the best moments of his career, with a huge Madison Square Garden pop. WWE pushed Triple H as the top face afterwards with a huge WrestleMania 18 WWE Championship win.

The plans for Triple H to have a strong face run as champ ended after a few weeks. Hulk Hogan and The Rock stole the show the same night Triple H won the title. WWE went with Hogan beating Triple H to build off his momentum, to end Triple H’s big run early, in embarrassing fashion.

8 Cutting Off Ric Flair's HOF Speech

The bond between Triple H and Ric Flair made it fitting that Triple H inducted Flair into the 2008 WWE Hall of Fame class. Flair delivered a long speech that Vince McMahon wanted to end as the show was running longer than anticipated.

Triple H was standing on the stage for Flair’s speech, and was the one informed to deliver the news that Flair needed to wrap his speech up quickly. Fans booed when Triple H walked to Flair and pointed to his watch to let him know the orders of the boss. Triple H admitted it was a horrible moment for him since Flair was his close friend and wrestling hero.

7 Wrestlers Walking Out On Him

In the aftermath of the Summer of Punk, Triple H replaced Vince McMahon as the head authority figure running the show. The roster grew uncomfortable with a hostile workplace environment, as a result of the dastardly actions going down under Triple H’s watch.

Most of the wrestlers walked out on Triple H during a storyline that made him look pretty foolish. Triple H’s time in this role did not go well, as the CM Punk feud went downhill and this was another embarrassing angle to end this chapter, with Vince eventually replacing him.

6 Pose Off With Scott Steiner

The signing of Scott Steiner made him a top face looking to feud with Triple H for the World Championship right away. Fans were excited for the program, but the two had zero chemistry, leading to horrible matches and segments.

The low point of the feud saw them facing off in a pose off since both men took pride in their physiques. WWE struggled to build momentum for Triple H vs Steiner, and watching them pose for five minutes just made the issue even worse.

5 Teaming With Shawn Michaels Vs. The Brothers Of Destruction

WWE tried to create special attraction matches for the shows in Saudi Arabia due to the money involved. Shawn Michaels came out of retirement for one more match, teaming with Triple H against The Undertaker and Kane.

All four legends had star power, but they were over the hill, leading to an all-time bad performance. The Last Ride documentary showed backstage footage of all the wrestlers feeling ashamed of their terrible outing, especially with Triple H revealing it was a disaster.

4 Booker T Promos

Fans still talk about some of Triple H's most offensive comments during a feud with Booker T. Triple H claimed that Booker and “people like him” were not meant to have top spots with racial implications involved.

The promos were horrible even for the time and it looked even worse since Booker lost the WrestleMania XIX match. Triple H did interviews at the time denying any ties to racial elements, but he said a few lines that clearly stated otherwise while crossing the line. The fact that he never got his comeuppance made this so much worse.

3 Getting Booed After A Match With Brock

Brock Lesnar returning to WWE in 2012 led to a dream match with Triple H, which was their first single's bout together. SummerSlam was main evented by the attraction, with Brock winning the disappointing match.

The post-match segment saw Triple H in the ring selling an injury and trying to get an ovation from the crowd, as if it could be his last match. Many fans instead chose to boo loudly, making the moment come off poorly for Triple H at the time.

2 Getting Squashed By The Ultimate Warrior At WrestleMania

Ultimate Warrior and Triple H faced off at WrestleMania XII, before Triple H was a major star. The hope for Triple H entering the match was to put up a fight against the legend, before ultimately taking the loss as many expected him to.

However, it was a huge disappointment for him, as he got completely squashed. Warrior had no desire to take any bumps or to sell for Triple H, so it turned into a squash match. Triple H spoke out against Warrior for years, until moving up to management and bringing him back to the company.

1 Katie Vick Segment

Triple H’s feud with Kane over the World Championship led to the backstory of Kane’s teenage girlfriend Katie Vick coming into play. Triple H revealed that Katie passed away after a car accident, where Kane had been behind the wheel.

However, there was a segment with Triple H wearing a Kane mask, claiming this was footage of Katie’s funeral. Triple H got into a casket and humped a mannequin pretending to be Kane in one of the worst segments in WWE history. The worst part was that they filmed it in an actual funeral home, with a real funeral going on in the room next door, according to Triple H.

NEXT: 10 Feuds Triple H Won That He Should've Lost